Film: Body of Lies
Year: 2008
Signature Look: Hypebeast of Arabia (technically Iraq, but whatever)

Leo had been running around Africa in Blood Diamond decked in ho-hum safari gear, but in Body of Lies CIA agent Roger Ferris pops up in Iraq wearing this amazingly streetwear-appropriate ensemble. The chambray bucket hat, navy vest with corduroy yoke, and numbered long sleeve shirt look like they came out of a street style post. The graphic placement on that shirt wouldn't seem out of place if say, Hood By Air printed a similar version. And the sunglasses? Those totally give him a Hunter S. Thompson vibe. Ferris' streetwear moment take an otherwise tepid film and make it a little more awesome.